Presented by Cole Haan
Even though today's work and life reality is more flexible than you think, managing our day-to-day in a 24/7 economy can still be a challenge. As the founder of Flex+Strategy Group, a growing business that helps create a flexible work culture for clients, and as a woman with two kids and a husband, I face the same array of seemingly endless choices many other women encounter: Where and when do I finish this presentation most productively? When will I be able to attend one of my daughter's field-hockey games? When can I get a haircut? Then there are bigger life transitions, like the pregnancy that caused one of my clients, a rising star at an investment bank who loved her job, to question her ability to have a career and a family. But the truth is, whether we work in an office or remotely, full-time or on a project basis, in-person or online, creatively rethinking how, when, and where we get our jobs done can offer countless opportunities for extraordinary women to turn what can feel like obstacles into triumphs.
First, we have to rid ourselves of the limiting, all-or-nothing mind-set that says it's either "this or that." There are many ways for you to earn money and manage your life throughout your career. It begins by recognizing that each of us has a different set of circumstances at any given time — there is no one right way to do it, except to keep learning and adapting as we go.
For me and for my clients, that recalibration of how work and life fit together can simply happen week to week. Even a bigger reset, like the one I guided the aforementioned banker through, might have an outcome that surprises you. As she was expecting her third child, she presented a plan to work four days a week, one of those days remotely. I wasn't surprised when her manager agreed, but she was. Today, this woman has three happy, healthy children and is a C-suite leader of the U.S. division of a global bank. When I see her, she will often say, "I can't believe I almost walked away."
Here, I answer Lenny readers' questions about how to live and work with strategic intention so you, too, can be your best self at work and at play.
Q: I've been out of college and working since 1993 in the same job: print-media sales. Four years ago, I quit my job of nineteen years to alter my career path. I'm willing to start at the bottom and take a pay cut to make this shift, but I don't know how to get someone to take a chance on me. How do I start over at 47 when most companies want to hire twentysomethings?
Cali Williams Yost: Let's start with your belief that companies are hiring only millennials. It's common when we have to make a big change that we get in a false narrative, that you think one thing when the reality is something different. In this case, you've convinced yourself that companies are hiring only millennials, which then infers they are not hiring you because you're 47. Yes, companies are hiring millennials — they have something to bring to the table. But somebody who has nineteen years of experience is also valuable to an organization.
The key question any company wants answered is: How can you help me get this job done well? You have to take a step back and say, "What is it that I'm bringing to the table?" Now, you don't want to be in print-media sales, but every single organization has to sell. Selling is an art and a science — it's not easy. You could go in and say, "Hey, I want to get into this new industry. Let me bring my sales understanding to the table to help your business thrive." You could start on a project basis and make a little bit of money, show your value, see if you like them.